JEE Advanced Previous Year Questions on Hydrocarbons

Question 1. In the following reactions compound x is;

Solution: (C)

The compound X is 2-phenylethanol.

The triple bond of ethynylbenzene is selectively hydrogenated to double bond by using Lindlar's
catalyst to obtain styrene.

Hydroboration oxidation of styrene gives 2-phenylethanol (compound X).

Question 2. In the following reactions compound y is;

Solution: (D)

Question 3. Isomers of hexane, based on their branching, can be divided into three distinct
classes as shown in the figure.
The correct order of their boiling point is

A. I > II > III

B. II > III > I

C. III > II > I

D. III > I > II

Solution: (C)

More the branching in an alkane, lesser will be the surface area, lesser will be the boiling point
as weaker will be the intermolecular attractive forces.

Question 4. The bond energy (in kcal mol-1) of a C−C single bond is approximately:

A. 1

B. 10

C. 100

D. 1000

Solution: (C)

C-C single bond dissociation energy range is between 88 to 150 Kcal mol1-1

C-C bond energy = 348J/mol = 348 / 4.2 kcal/mol

= 82.85 kcal/mol

≈ 100 kcal/mol

Question 5. The total number of stereoisomers that can exist for M is:
Solution: (2)

The total number of stereoisomers is 2.

This molecule can not show geometrical isomerism so only mirror image will be other stereoisomer.

Question 6. The total number(s) of stable conformers with non-zero dipole moment for the
following compound is (are):

A. 2
B. 4

C. 3

D. 5

Solution: (C)

Three stable (staggered) conformers exist (with μ≠0)

Note: Two or more structures that are categorized as conformers differ only in terms of the angle about
one or more sigma bonds.

Question 7. Newman projections P, Q, R and S are shown below:

Which one of the following options represents identical molecules?

A. P and Q

B. Q and S

C. Q and R

D. R and S

Solution: (C)
Question 8. On monochlorination of 2-methylbutane, the total number of chiral compounds
obtained is.

A. 2

B. 4

C. 6

D. 8

Solution: (A)
During the monochlorination of 2 methyl butane, four compounds are possible however only two of
them will be chiral in nature. Here, I and III are chiral.

Question 9. Which of the following reaction produce propane as a major product?

Solution: (B and C)
Question 10. The correct statement(s) for the following addition reactions is(are):

A. O and P are identical molecules

B. (M and O) and (N and P) are two pairs of diastereomers

C. (M and O) and (N and P) are two pairs of enantiomers

D. Bromination proceeds through trans-addition in both the reactions

Solution: (B and D)

(B) (M and O) and (N and P) are two pairs of diastereomers. They have the same configuration at one
chiral carbon atom and a different configuration at other chiral carbon atoms.
(D) Bromination proceeds through trans-addition in both reactions. It involves the formation of cyclic
bromonium ions.